Electrochemical synthesis and studies of substituted 2-thiopyridines

Кайгородова, E. А.; Konyushkin, L. D.; Niyazymbetov, M. E.; Kvak, S. N.; Zaplishny, V. N.; Литвинов, В. П.

doi:10.1007/bf00700178

Cited by 6 publications

(5 citation statements)

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“…To further develop our studies on the alkylation of 6-methyl-4-methoxymethyl-3-cyano-2(1H)-pyridinethione (1a) and its structural isomer 1b [4][5][6], the pyridinethiones 1a,b were reacted with 5-nitro-furylmethyl-and 4-nitrobenzyl bromides and the 5-chloromethyl derivative of methyl 2 furoate (Scheme 1). …”

Section: Resultsmentioning

confidence: 99%

“…A mixture of pyridinethione 1a [5] (1.94 g, 10 mmol) in DMF (20-25 mL), 4-nitrobenzyl bromide (2.16g 10 mmol) and a 10% aqueous solution of KOH (5.6 mL, 10 mmol) was kept at r.t for 2h, then diluted with water (10 mL). The precipitate formed was filtered off, washed with water, dried and recrystallized from ethanol to give 3.03 g (92%) of 3a.…”

Section: -Methyl-4-methoxymethyl-3-cyano-2-(4-nitrobenzyl)thiopyridimentioning

confidence: 99%

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Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

et al. 2000

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Section: Resultsmentioning

confidence: 99%

Section: -Methyl-4-methoxymethyl-3-cyano-2-(4-nitrobenzyl)thiopyridimentioning

confidence: 99%

Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

et al. 2000

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“…To a mixture of 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile , or 4-(methoxymethyl)-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile (20 mmol) and 10% aq. KOH solution (11.2 mL, 20 mmol) in DMF (20 mL), the corresponding N -aryl-2-chloroacetamide (20 mmol) was added.…”

Section: Experimental Sectionmentioning

confidence: 99%

Unusual Oxidative Dimerization in the 3-Aminothieno[2,3-b]pyridine-2-carboxamide Series

et al. 2021

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Noncatalyzed, regio-and stereoselective hypochlorite oxidation of 3-aminothieno[2,3-b]pyridine-2-carboxamides is presented. Unexpectedly, the oxidation proceeded by different mechanistic pathways, and different products were formed, depending on the nature of solvents used. A possible mechanism, the structure of products, kinetics and dynamics of intramolecular processes, and biological activity of products are discussed.

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“…Pyridines 4a and 4e have already been prepared and some of their properties have been reported in our previous work [4,5].…”

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Synthesis and properties of (thieno[2,3-b]pyridin-3-yl)iminotriphenylphosphoranes. Molecular structure of (2-benzoyl-4-methoxymethyl-6-methylthieno[2,3-b]pyridin-3-yl)iminotriphenylphosphorane

Кайгородова

Vasilin

Lipunov

et al. 2004

Chem Heterocycl Compd

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Iminophosphoranes, in light of their electronic structure, are promising intermediates for the synthesis of many compounds of different types [1][2][3]. In the present work, we synthesized thieno[2,3-b]-pyridinyliminophosphoranes, for which no data have been available in the literature, and studied the physicochemical properties of these compounds.Pyridinethione 1, α-haloacetic acid derivatives 2a-d, and phenacyl bromide 2e served as the starting compounds for the preparation of (thieno[2,3-b]pyridin-3-yl)iminotriphenylphosphoranes.The reaction of pyridinethione 1 with α-halocarbonyl compounds 2a-e were carried out in the presence of two equivalents of KOH to bind the hydrogen halide liberated and provide for the Thorpe-Ziegler isomerization of intermediate S-alkyl derivatives 3a-e to give 3-aminothieno[2,3-b]pyridines 4a-e (Scheme 1).3-Aminothieno[2,3-b]pyridines 4 are bright-yellow compounds, which are highly soluble in polar solvents (Table 1). Pyridines 4a and 4e have already been prepared and some of their properties have been reported in our previous work [4,5].The structure of the 3-aminothieno[2,3-b]pyridines was confirmed by IR, UV, and 1 H NMR spectroscopy ( Table 2). The IR spectra of 4a-e lacked the nitrile group band at 2210 cm -1 and thioamide group band at 1215 cm -1 characteristic for starting pyridinethione 1 but have stretching bands for the amino group N-H bond at 3465-3400 and 3330-3255 cm -1 as well as stretching bands for the conjugated carbonyl group in ester 4a __________________________________________________________________________________________

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Electrochemical synthesis and studies of substituted 2-thiopyridines

Cited by 6 publications

References 1 publication

Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

Unusual Oxidative Dimerization in the 3-Aminothieno[2,3-b]pyridine-2-carboxamide Series

Synthesis and properties of (thieno[2,3-b]pyridin-3-yl)iminotriphenylphosphoranes. Molecular structure of (2-benzoyl-4-methoxymethyl-6-methylthieno[2,3-b]pyridin-3-yl)iminotriphenylphosphorane

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